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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:59 UTC
HMDB IDHMDB0014617
Secondary Accession Numbers
  • HMDB14617
Metabolite Identification
Common NameMethohexital
DescriptionMethohexital is only found in individuals that have used or taken this drug. It is an intravenous anesthetic with a short duration of action that may be used for induction of anesthesia. [PubChem]Methohexital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Structure
Data?1582753199
Synonyms
ValueSource
(+-)-5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)barbituric acidChEBI
5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-Allyl-1-methyl-5-(1-methyl-pent-2-ynyl)-pyrimidine-2,4,6-trioneChEBI
5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbituric acidChEBI
alpha-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbituric acidChEBI
MethohexitalumChEBI
MethohexitoneChEBI
MetohexitalChEBI
(+-)-5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)barbitateGenerator
(+-)-5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)barbitic acidGenerator
5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbitateGenerator
5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbitic acidGenerator
a-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitateGenerator
a-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitic acidGenerator
alpha-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitateGenerator
alpha-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitic acidGenerator
Α-DL-1-methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitateGenerator
Α-DL-1-methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitic acidGenerator
MethodrexitoneHMDB
BrevitalHMDB
Sodium, methohexitalHMDB
BrietalHMDB
Lilly brand OF methohexital sodiumHMDB
Methohexital sodiumHMDB
Brietal-sodiumHMDB
Brevimytal natriumHMDB
Jones brand OF methohexital sodiumHMDB
Methohexital, monosodium saltHMDB
Monosodium salt methohexitalHMDB
Natrium, brevimytalHMDB
Brietal sodiumHMDB
Chemical FormulaC14H18N2O3
Average Molecular Weight262.3043
Monoisotopic Molecular Weight262.131742452
IUPAC Name5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
Traditional Namemethohexital
CAS Registry Number151-83-7
SMILES
CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O
InChI Identifier
InChI=1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)
InChI KeyNZXKDOXHBHYTKP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentBarbituric acid derivatives
Alternative Parents
Substituents
  • Barbiturate
  • N-acyl urea
  • Ureide
  • 1,3-diazinane
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.052 g/LNot Available
LogP1.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP2.43ALOGPS
logP2.29ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity71.51 m³·mol⁻¹ChemAxon
Polarizability27.4 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-4390000000-8c577a429e1b4575b629Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2090000000-43730b3bde391b731ebeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-3970000000-fc9a91490da8afc576f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9x-9000000000-93587b41eae6b9864e81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2920000000-ad50a444d0a4a9a5af2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-4910000000-c5dc261173ac7024e26fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-7cedeac5d5e1a5954aa4Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fbc-9520000000-5141cdceea7f6d5013b0Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00474 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00474 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00474
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8683
KEGG Compound IDC07844
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethohexital
METLIN IDNot Available
PubChem Compound9034
PDB IDNot Available
ChEBI ID102216
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Koltchine VV, Ye Q, Finn SE, Harrison NL: Chimeric GABAA/glycine receptors: expression and barbiturate pharmacology. Neuropharmacology. 1996;35(9-10):1445-56. [PubMed:9014160 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]